(4S)-4-[(3S)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxybutyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

Details

• Internal ID: 06c0518d-f777-455f-90a9-17fb71d0865b
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acyl glycosides > Fatty acyl glycosides of mono- and disaccharides
• IUPAC Name: (4S)-4-[(3S)-3-[(2R,3R,4S,5S,6R)-6-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxybutyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one
• SMILES (Canonical): CC1=CC(=O)CC(C1(CCC(C)OC2C(C(C(C(O2)COC3C(C(CO3)(CO)O)O)O)O)O)O)(C)C
• SMILES (Isomeric): CC1=CC(=O)CC([C@]1(CC[C@H](C)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@@H]([C@](CO3)(CO)O)O)O)O)O)O)(C)C
• InChI: InChI=1S/C24H40O12/c1-12-7-14(26)8-22(3,4)24(12,32)6-5-13(2)35-20-18(29)17(28)16(27)15(36-20)9-33-21-19(30)23(31,10-25)11-34-21/h7,13,15-21,25,27-32H,5-6,8-11H2,1-4H3/t13-,15+,16+,17-,18+,19-,20+,21+,23+,24+/m0/s1
• InChI Key: VXZUZURNJDKPBW-NOHNOBMDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₄₀O₁₂
• Molecular Weight: 520.60 g/mol
• Exact Mass: 520.25197671 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -1.89
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6175	61.75%
Caco-2	-	0.8294	82.94%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8605	86.05%
OATP2B1 inhibitior	-	0.7195	71.95%
OATP1B1 inhibitior	+	0.8774	87.74%
OATP1B3 inhibitior	+	0.8696	86.96%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.6475	64.75%
P-glycoprotein inhibitior	-	0.5523	55.23%
P-glycoprotein substrate	-	0.5783	57.83%
CYP3A4 substrate	+	0.6947	69.47%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8858	88.58%
CYP3A4 inhibition	-	0.9154	91.54%
CYP2C9 inhibition	-	0.8381	83.81%
CYP2C19 inhibition	-	0.8933	89.33%
CYP2D6 inhibition	-	0.9260	92.60%
CYP1A2 inhibition	-	0.9122	91.22%
CYP2C8 inhibition	-	0.7534	75.34%
CYP inhibitory promiscuity	-	0.9270	92.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6233	62.33%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9579	95.79%
Skin irritation	-	0.6021	60.21%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4084	40.84%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.7070	70.70%
skin sensitisation	-	0.8838	88.38%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5470	54.70%
Acute Oral Toxicity (c)	III	0.4667	46.67%
Estrogen receptor binding	+	0.6176	61.76%
Androgen receptor binding	+	0.5858	58.58%
Thyroid receptor binding	+	0.5545	55.45%
Glucocorticoid receptor binding	+	0.5614	56.14%
Aromatase binding	+	0.7516	75.16%
PPAR gamma	+	0.6110	61.10%
Honey bee toxicity	-	0.7974	79.74%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9421	94.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	98.92%	83.57%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.87%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.82%	95.93%
CHEMBL2581	P07339	Cathepsin D	95.94%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.76%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.84%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.03%	96.09%
CHEMBL220	P22303	Acetylcholinesterase	92.84%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.68%	99.23%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.46%	96.47%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.47%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.81%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.57%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.40%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.69%	95.89%
CHEMBL4581	P52732	Kinesin-like protein 1	84.54%	93.18%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.46%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.41%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.96%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.75%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	83.65%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	82.30%	94.73%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.51%	95.71%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.07%	97.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.85%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.52%	90.71%

Plants that contains it

• Casearia sylvestris

Cross-Links

• PubChem: 44130495
• LOTUS: LTS0193746
• wikiData: Q105298852